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I traveled for work at a previous job, and we fly often for vacations. Below are my tips and notes to myself for how I travel. I hope these might be useful for you, too!

Flights and frequent flyer miles

I heavily lean towards direct flights, to reduce the likelihood that I'm stuck at a layover. For Seattle, that means that I almost always check Alaska Airlines first–their hub is SeaTac.

Back when we lived in Blacksburg, Virginia, we'd drive down to Charlotte rather than flying out of Roanoke to take direct flights.

If my dates are flexible, I use Alaska's "flexible dates" service to see the cost by day.

Mileage plans

I never really understood mileage plans and how to think about them until I traveled for work. It varies from airline to airline, but for Alaska at least 1 mile is roughly 1 cent.

Alaska Airlines has options for using miles:

  • Miles pay for the whole flight
  • $200 off for 20,000 miles
  • $100 off for 10,000 miles

I will often do the $100 or $200 off; you still earn miles with that option.

We also have the Alaska Airlines credit card, which (a) accrues miles as you use it, (b) gives you an annual companion fare for roughly $121, and (c) gives you one free bag per person. The annual fee for this card is $79; essentially, you're getting a $200 companion fare once a year. I use this card to buy the plane tickets because you get extra miles when you buy tickets.

TSA pre-check

If you fly a lot and are OK with the privacy issues, you can pay for TSA pre-check or alternatively Global Entry. Global Entry gives you TSA pre-check. If you have pre-check then you can save half an hour sometimes at the security check-in.


If I'm traveling on my own I try to carry everything in a carry-on. Otherwise, I use the free bag per person to check bags. Bags can weigh up to 50 lbs.

Also, I'm sure it depends on the airline but on Alaska bags are constrained by a maximum total length plus width plus height. Beyond that they can be in whatever shape. As a result, I've sent cardboard boxes through as baggage.


If the airport parking is expensive, most airports have good private parking services nearby. The one we currently use for SeaTac lets you pre-pay for your parking on-line ahead of time, which gives you free parking days as well as an on-line discount.


I have a Tripit account and I email all the plans I make to This lets me see my itinerary and also share my itinerary with others as I see fit.


I don't know enough about hotels to use their membership rewards. I've found the membership that I had expired really quickly if I didn't stay at the same hotel every time.

That said, I try to check ahead of time for whether there's a charge for parking. I also try to look at the star rating and how easily I can walk to places, in addition to the cost. If I can walk to where I'm going, then I won't need to spend as much money on taxis/rental cars.

Stuff maybe needed

Transit pass

If wherever I'm going has good public transit, I look it up ahead of time to see if I could take it from the airport to wherever I'm staying. I also look up whether there's a day or a week pass option that I could buy at the airport.

Rental car

If I only need to drive a little–like only on certain days or only to certain destinations–it may be cheaper to use Lyft than to rent a car.

If I still need a car, if I have any benefit that gives me a "membership" then I'll look at those services first. For example, I had an "Emerald Club" membership through a credit card–this let me go straight to the car and drive it away without having to wait.

Regarding insurance, my car insurance will cover liability but not necessarily collision/comprehensive. One of my credit cards does cover collision/comprehensive. I try to use this card.

Sometimes rental car companies will give you a mileage benefit–I have mine set to go to my airline miles.

Offline maps

If wherever I'm going has poor/nonexistent cell phone service (e.g. Alaska), then I download maps ahead of time using Google offline maps.

Pre-trip planning: pets

A month or more ahead of time, I book visits with our pet care service to ensure our cats get fed.

A week or more ahead of time, I ensure we have enough food and litter.

Work checklists

I keep a "pre-" and "post-vacation" checklist for work.

Before vacation

  • Identify my backup while I’m gone & let my manager know
  • Ask my manager to do student timecard approvals
  • Set OOO (out of office) message. mention who to email while I'm out.
  • Email team a reminder that I'll be out.
  • Review tasks for while I'm gone. Since I use org-mode, I do this via

    C-c a m
  • turn off phone notifications (Slack, Outlook)
  • set Slack status
  • on phone, turn off Slack online: settings > availability
  • check Jira
  • Make sure office windows are closed
  • Block time for when I come back to deal with vacation stuff
  • set voicemail: voicemail website URL -> personal settings ->

    Hello, this is John Borwick. I am out of the office until __. Please consider emailing me at [my email address]. Otherwise, please leave a message, and I will return your call when I am back in the office.

  • turn off computers

After vacation

  • reinstall Outlook, Slack on phone
  • confirm HR system up to date
  • unset voicemail: voicemail website URL -> personal settings
  • turn on phone notifications
  • unset Slack status
  • phone: turn on Slack online: settings > availability
  • create task for writing up conference report (if I was at a conference)

Review memberships

We have a couple of membership, e.g. a membership to the Pacific Science Center, that have reciprocal memberships in other locations.

Pack list

I don't have a great pack list. That said, my rough categories are:

  • Wallet: I remove extra cards and I try to have some cash, including small bills for tips
  • Phone
  • Computer bag (I have the Tom Binh "Cambiata" bag)
    • Computer and computer power
    • USB-C adapters for charging watch and Kindle
    • Nalgene water bottle
    • Snack bars
    • Pens and notebook
    • Reading materials: magazine, book, Kindle
    • Earbuds
    • Phone adapter (to use earbuds)
    • Phone charger
    • Gum
    • Keys/other items I don't need until I return home: these go into a special pocket
  • Large bag (I have a Timbuk2 soft-shell suitcase)
    • Clothes
    • Toiletries
    • Inflatable meditation cushion
    • Other books
    • Laundry bag

I use the hotel's iron to iron clothes rather than trying to keep them from getting wrinkled in my bag.

Special pack list items

Depending on the circumstances, I may also want to take:

  • Hat
  • Sandals
  • Sunblock
  • Sunglasses
  • Swim trunks